Most startup advice breaks down right when it’s needed most, in the messy middle, after the first signs of traction and before real scale. This is the phase where dashboards look decent, investors get excited, and founders quietly wonder if they’re about to make the wrong irreversible decision.
Karen Page has lived in that middle for decades.
Before becoming a General Partner at B Capital, Karen helped scale Box from its early days, built one of the most influential partnership ecosystems in SaaS, and later led enterprise go-to-market strategy at Apple. Today, she sits on boards and works directly with founders navigating the exact moment where momentum can either compound or collapse.
This episode isn’t about hype cycles or shortcuts. It’s about how companies actually grow.
Scaling is a mindset shift, not a milestone
One of Karen’s core observations is simple and uncomfortable. The skills that get a company from zero to one are not the same skills that get it from one to ten.
Early traction rewards speed and conviction. Scale rewards clarity and judgment.
Founders who struggle during this transition often don’t lack intelligence or ambition. They lack perspective. They are deep in the weeds, fighting fires, optimizing tactics, and missing the broader terrain. Karen describes her role as oscillating between airplane mode and ant mode. Most of the time, she’s zoomed out, scanning for patterns, risks, and opportunities. Occasionally, she dives deep to help solve a specific problem that’s blocking progress.
Great founders learn to do the same.
Go-to-market clarity beats tactics every time
Tools change. Channels change. AI changes everything around the edges.
What doesn’t change is the need for an undeniable value proposition.
Karen has seen every GTM flavor, sales-led, partnerships, product-led growth, enterprise-heavy motions, and now AI-assisted everything. Her conclusion is blunt. If you cannot clearly articulate what you sell, who it’s for, and why it materially changes how that customer operates, no GTM motion will save you.
Founders often over-rotate on tactics when growth slows. New hires. New pricing. New tools. What’s usually broken is the message.
Clarity compounds. Confusion leaks.
Boards are leverage, not overhead
Many early founders delay forming a board because they fear bureaucracy or loss of control. Karen takes a more pragmatic view.
A board is not about governance theater. It’s about access to pattern recognition.
The best boards function as a room of trusted advisors who have seen similar problems before, often at the worst possible moments. Hiring mistakes. GTM stalls. Executive transitions. Strategic forks in the road. These moments don’t show up neatly on dashboards, but they determine outcomes.
Her guiding principle is “noses in, fingers out.” Boards should be deeply curious, strategically engaged, and respectful of the operator’s role. When trust exists, hard conversations become productive instead of destructive.
AI is a bigger shift than cloud ever was
Karen lived through the cloud transition firsthand. She sees AI as something fundamentally larger.
Cloud changed where software lived. AI changes how work itself is done.
The opportunity isn’t just efficiency. It’s redefinition. Entire workflows, pricing models, and operating assumptions are being rebuilt in real time. Companies that treat AI as a feature risk irrelevance. Companies that rethink processes from first principles gain unfair advantage.
This shift also changes how founders think about scale. Capital efficiency is improving. Smaller teams are doing more. Value per employee is becoming a critical metric. The winners won’t just grow faster. They’ll grow smarter.
Vertical software is quietly getting dangerous
One of Karen’s most contrarian views is her continued conviction in vertical software.
For years, many vertical markets looked too small to support venture-scale outcomes. AI changes that math. When software starts absorbing labor, not just software budgets, it can capture a much larger share of economic value within a niche.
The result is deeply specialized companies solving real problems with precision, not generic platforms trying to be everything to everyone.
These businesses don’t look flashy at first glance. They compound relentlessly.
The founder skill that matters most
Across all stages, industries, and cycles, Karen keeps coming back to the same trait.
Curiosity.
The best founders are relentless learners. They seek data, ask uncomfortable questions, pressure-test their assumptions, and update their thinking when reality changes. They don’t confuse confidence with rigidity.
That learning mindset is what allows founders to scale themselves alongside their companies. Without it, growth eventually stalls.
The long game
Karen’s definition of success isn’t just ringing the bell at an IPO, though she’s done that too. It’s helping build companies that last because the leadership, culture, and decision-making systems were strong enough to survive inevitable stress.
The throughline of her career is partnership. Connecting people, systems, and ideas so the whole becomes greater than the sum of its parts.
In a world obsessed with speed, that might be the most durable advantage of all.
If you’re a founder navigating the jump from early traction to real scale, this conversation is a reminder that the hardest problems are rarely tactical. They’re structural, human, and strategic. And they show up whether you’re ready or not.
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Chapters:
00:01 Welcome and Karen Page’s background
02:30 Early career in sales and building GTM foundations
04:20 Discovering partnerships as a growth lever
06:00 Scaling Box through ecosystem strategy
08:10 Exposure to venture while fundraising at Box
10:00 Transition from operator to investor
12:00 Why B Capital and building the early-stage fund
14:30 How Karen works with founders and boards
17:00 What great founders do differently as they scale
19:45 Evaluating investors and building the right board
22:00 Boardroom trust and decision-making under pressure
25:20 AI as a platform shift versus cloud and mobile
28:00 Go-to-market evolution in an AI-first world
31:00 Pricing, value creation, and capital efficiency with AI
34:00 Product-led growth versus sales-led at scale
36:30 Vertical software and overlooked markets
39:30 Talent, culture, and scaling leadership
43:00 How venture and startups will evolve
46:30 Timeless GTM principles and founder lessons
Transcript
Brian Bell (00:00:59):
Hey, everyone. Welcome back to the Ignite podcast. Today, we’re thrilled to have Karen Page on the mic. She’s a general partner at B Capital Group and one of the most accomplished go-to-market leaders turned investors in venture. Before B Capital, Karen was a founding executive at Box, where she built out the partnership ecosystem and founded Box.org. Very cool. She later joined Apple, leading enterprise partnerships and GTM strategy. Today, she sits on or advises multiple boards across SaaS, fintech, and digital health, helping founders turn early traction into scale sustainable growth. Thanks for coming on, Karen.
Karen Page (00:01:29):
Thank you so much. It’s really good to be there.
Brian Bell (00:01:31):
Yeah, likewise. So I would love to get your origin story for the listeners.
Karen Page (00:01:35):
Absolutely. I grew up in a little town outside of Annapolis, Maryland, oldest of six kids, ran around a bunch in that area and kind of decided by the time I was in 11th grade that I was ready to go to college. So I figured out how to work the system, graduated early, landed at Towson State, barely 17 years old at the time and did exactly what I had always known I wanted to do, which was major in business. I jumped out of Towson after four years and got a job in sales. And I really believe that that was a very strong foundation. I didn’t imagine myself in sales and yet that’s where I landed. It was an incredible experience for me, really solidified kind of how to build relationships and really had a great time. I also knew that I was not going to stay in Baltimore for the rest of my life and started preparing for my eventual exit. I knew that I would need a great kind of master’s degree. So started working at night towards a degree at Johns Hopkins in their, what was now called the Cary Business School at the time was just Johns Hopkins Executive Program in Business and worked my way through that program. At the time that I was just about to graduate, I was working on my thesis there and got an opportunity to move to Honolulu, Hawaii. I was just getting married and had an opportunity to transfer with my sales role and took that and I was an avid runner, avid triathlete, greatest place in the world to take on those activities and continued my sales effort. A few years later, migrated over to LexisNexis, which was awesome. That was at the time when they were transitioning to web-based solutions. I was selling into law firms and took over Hawaii for them, incredible experience. 99, 2000 era, had an opportunity to move to the Bay Area, which was also kind of a big dream of mine, just as things were getting crazy and heated up there. I moved there in about 2000, got the bug for startups, but was also going through a transition in my life. I had two small children, was going through divorce and needed to kind of have a job that would allow me to both be a mom, and kind of have my foot in the career world. So I landed at Brobeck, worked as a marketing lead there for the business team. It was also a really incredible time. Transitioned from there to Orrick, Herrington and Sutcliffe, where I built business development programs for the lawyers there, all the partners. And that led me to my first startup, which was called Prosper. And under Chris Larsen, who was just a great, great leader, very disciplined. And eventually, just maybe a year or two later, was introduced to Aaron Levy at Box. And that was not only the most incredible career experience I think I’ve ever had, but also really where I got foundational insights and growth into how to build something big.
Brian Bell (00:04:27):
Amazing journey. A lot of parallels, actually. Yeah, I lived in Honolulu as well, but it was 2008 to 2011, before I came to the Bay Area. So I also left Honolulu to come to the Bay. So that’s pretty wild.
Karen Page (00:04:37):
Such a great place.
Brian Bell (00:04:39):
Yeah, I wanted to work in solar. That’s why I came to the Bay Area and I ended up in tech, but long story. So yeah, lots to unpack there. Let’s talk about when you first realized you had this talent for connecting companies through partnerships or how you developed that.
Karen Page (00:04:53):
Some of it I think was just instinct. It certainly is one of the clearest through lines in my entire career is putting things and people together so that they’re bigger than their independent parts. And this idea of partnerships has really shaped every chapter of my life, from building the partner ecosystem at Box to landing at Apple and helping them to secure a more complicated set of strategies. But I think partnerships are kind of like puzzles. And I definitely love a good puzzle. It’s about being able to see how pieces fit together to create something bigger and better. One example was when I was at Box. I was talking with the head of partnerships at NetSuite. And they had, you know, kind of this antiquated locker for documents behind the scenes that all of their customers were using. It was ineffective. It wasn’t worth rebuilding for them. So we did a tight integration with Box. We became their content manager. And it was a fantastic partnership. It really enabled them to create a suite of services that made NetSuite better. And certainly for Box, it was a way to incorporate into a very well-known leader at the time. So that’s just just kind of one example of how I would think about things. How can one plus one equal three? And then of course you have to go behind the scenes and figure out how to make the teams kind of cohabitate in a way that would leverage sales for both parties.
Brian Bell (00:06:17):
Another parallel, I ran partnership teams at AWS and Azure and Microsoft. So very familiar, you know, trying to make one plus one equal three. Didn’t always succeed, but very familiar with that notion.
Karen Page (00:06:29):
Yeah. Yeah. Yeah. And then, you know, at Apple, it was really about how do we, how do we leverage, you know, our clients and the people who are buying Apple products who also were clients of SAP or IBM to build applications that helped them to leverage their success as well. So, you know, that just kind of became, you know, how do you build transformative applications that help businesses grow through channel partners? And, you know, that was a, that was an incredibly fun experience as well.
Brian Bell (00:06:58):
And at some point, and we’re glossing over a lot of detail here and moving pretty quickly, but got into venture capital. What was that transition like?
Karen Page (00:07:06):
So it was another era. You know, I always joke that I manifested my role at Box. I wanted to in my, you know, kind of my thrilled excitement around startups and that whole business. You know, I decided that I wanted to go to a startup at the earliest stage and go all the way through the exit. And, you know, and I was lucky enough to meet Aaron and to join Box. And when I was at Box, when we were quite early in our progression, one of the roles that I took on was making sure that we knew every investor in the market. And so I spent a lot of time in front of VCs. And while I was growing the business and helping to raise money at Box, I saw what the VCs were doing and I became very enamored of that. And in my mind in those early days, I sort of began to manifest the idea that I would end my career in venture. Incredibly enough, that was what happened.
Brian Bell (00:08:05):
That’s interesting. So Aaron’s like, hey, go meet all the VCs. We’re going to have to raise an A or B or C or whatever it is. And so you’re meeting all these VCs and you kind of get sucked into it a little bit as you start meeting them and seeing what they do. And you’re like, what’s your job really? Just like meet founders? Oh, great.
Karen Page (00:08:21):
Yeah. I want to do that.
Brian Bell (00:08:23):
That sounds cool. And then you wire the money and then you help them? That sounds awesome. It sounds like the best partnership job ever.
Karen Page (00:08:30):
The best partnership job ever.
Karen Page (00:08:31):
And crazy enough, during my time at Box, I happened to hire this guy named Mike Cardamone. He wanted to launch his own venture fund, me and a couple other names you would know. Gave him a little bit of seed money to start. He brought us in as LPGPs on the headliner. And I became very active in Acceler Prize, which is now called Forum, bringing the founders on how to do great pitches and what should their strategy be. So I did get a ton of experience in working with very, very early pre-funded founders. founders on their structure and their strategy and their approach and how they sold their approach and all of that sort of stuff. So it gave me some really good experience.
Brian Bell (00:09:13):
So what finally convinced you to move into venture and why B Capital specifically?
Karen Page (00:09:18):
So a lot of it was just timing. I think I was at a point in my career where I felt like I had done big things and that I wanted to change my focus to really help other companies do great things. Many great companies do great things. And I felt like I had the aperture and the ability to see around corners from the experiences that I had. And I felt like I would be able to not only to spot good founders based on my experiences in working with so many people over the years, but also to really help them to grow and scale. So why B Capital? Well, I met Raj Ganguly. So B Capital was founded in 2015 by Raj Ganguly and Eduardo Saverin, who was one of the founders of Facebook. They very quickly brought Howard Morgan into the equation as our chairman, who was one of the founders with Josh Kaufman at First Round Capital. And they had just kind of a dream team and a great approach. It was a global growth stage company. They partnered with the Boston Consulting Group with the philosophy that as companies grow in scale, they’re going to hit inflection points where they’re going to need companies. kind of the access to the brightest minds in business that the BCG Group could provide to us, and that that would be an incredible platform on which to build. And it’s proven out. It’s been an incredible strategy. Since then, since I think I joined, we had about $360 million of assets under management. Today, we’re over $8.5 billion with several different funds that we operate out of. Howard and I launched the Early Stage Fund in late 2020, early 21. Our third partner, Gabe Greenbaum, And, you know, that gave us the ability to look a little earlier than growth. Super, super fun for me. I’m a builder. I loved helping to build the Ascent team and to help build B Capital as a whole. So it’s been an incredible experience.
Brian Bell (00:11:01):
Yeah. And so like how big is the early stage fund? What’s the thesis? Where do you guys like to enter ownership targets? How many checks are you guys writing? You always take importance. It’s all those. Tell me all the VC characteristics of the early stage fund.
Karen Page (00:11:14):
Yeah. So in our current fund, we’re thinking it’ll be somewhere around 40 checks. We like to take 10 to 15% ownership. We will take a board seat if that’s what the founder wants. Our whole premise is how do we provide access, resources, advice to the founder as they want it, noses in, fingers out, and really hoping to find ways that we’re working to help them grow. The scene has changed quite dramatically over the last couple of years. AI is driving everything. It certainly has impacted our thesis area. It’s an interesting intersection in check sizes because check sizes have changed pretty tremendously. That’s all something that we put into the hopper and start thinking about and figure out the right approach. We can be pretty flexible, which I really enjoy.
Brian Bell (00:12:03):
Yeah, that’s pretty. What do you mean by noses and fingers out? I’ve never heard that phrase.
Karen Page (00:12:07):
So I’ve been spending most of my time lately on our existing portfolio and the board seats there. So I have the portfolio of companies that I have invested in directly. And then I have some other companies that I’ve taken on in the past year or so. that are very late stage growth companies and working with them on growth. So I’m spending a lot of my time, less time investing more time on boards. Noses in, fingers out just means like you’re curious and you’re thinking and you’re working on problems, but you’re not poking into the CEO’s day-to-day business. You know, our job is the CEO, his job is the team. If he needs our help or if she needs our help, we’ll dive in. And that’s another kind of thing that I think about, which is airplanes and ants. So sometimes I’m an airplane, most of the time I’m an airplane, right? I’m looking at across the landscape and thinking about the strategy and working together with the founder on the big picture. But every once in a while, there’s a problem that demands that you dive in a little bit deeper. You’ve got to get involved. And hopefully that’s what I’m really good at. Hopefully that’s where I can look across the landscape, see something that looks like it’s either a great opportunity or a great problem and dive in a little bit deeper to work with the founder to hopefully make the best of it, whichever way it is.
Brian Bell (00:13:21):
Yeah. How do you think your background, operation background and your partnership backgrounds influenced your approach with founders today?
Karen Page (00:13:29):
So it’s a great question. I think that when I think about working with a founder, I want to understand the business. I want to be helpful to the extent that I can. And hopefully my background does provide some leverage and some insights. Also want to be able to bring in a bigger picture. A lot of times founders have their experience, what they’ve done, and they know how they need to do things. But They might have natural blind spots, which doesn’t at all mean that they aren’t great at what they’re doing. It just means like, oh, have you thought about this? Have you thought about that? So expanding the landscape to make sure that we’re covering all aspects as efficiently as possible. I can’t tell you how many times I see a founder, whether they’re one of our founders or someone that I encounter through the various networks, who is like, I want to do this. And I’ll say like, well, have you thought about doing it this way or that way as an alternative? Because I’ve seen a lot of things succeed and I’ve seen a lot of things fail. If there are ways that we can have those conversations and hopefully impact their ability to save time. I mean, everybody knows, you hire a sales leader, you might have you know, 50 to 60% hit rate the first time. That loss, if that doesn’t work out, that can cost a year. You know, nobody’s got that kind of time. So how can we make sure that the decisions that we’re making are the best and that they have taken in past failures and past successes to make the best decisions possible?
Brian Bell (00:14:56):
Yeah, that’s interesting. I’d love to turn that around too, as for the founders listening, how do they evaluate who they should bring on the cap table at these different stages?
Karen Page (00:15:04):
The lucky ones have their choice. And then there are other ones who have to go through the fundraising process, you know, pretty extensively to find the right fit. We hope that every founder gets to choose the exact investor they want to work with. However, that’s not always the case. It can work out to their benefit, and sometimes it doesn’t. We hope that every investor and every founder that work together find the cadence in their relationships, find the strength in their relationships, and are able to leverage what each investor brings to the table to kind of piece together the perfect board. We know that boards early on are going to be comprised of the investors around the room. So you hope that those are the right people to help guide your company forward. Most of the time they are. We do see sometimes when there are various crucible moments or sometimes we see misalignment on boards and those have to be addressed. But most of the time we see that happening in a way that that yields a positive outcome. It can be.
Brian Bell (00:16:04):
Yeah. So you’ve backed and advised many amazing companies. What are some commonalities that the best founders do differently as they kind of move from C to A to B?
Karen Page (00:16:14):
Yeah, I think the best founders have this amazing ability to learn. We’ve had so many people kind of go before us and you can leverage them. the writings and the experiences of other people to take the good and leave behind the bad. But the best founders I’ve ever seen are avid learners, curious. They want to know what works, what doesn’t, and they are willing to take other people’s point of view, assess it, and then make their own decisions as a result. I love that quality in almost anyone. The curiosity and the ability to learn is just going to take them, you know, pretty far, I believe.
Brian Bell (00:16:55):
How do you detect that in a founder when you’re getting to know them? Maybe, I know you’re not doing as much of investing these days, but like as you’re trying to assess that, for someone like me who’s in the pre-seed really, really early, right? And I’m meeting these founders, meeting lots of founders, and you’re kind of looking for superpowers, right? Something special about them, right? Like how are you kind of sussing that out?
Karen Page (00:17:16):
I think it comes out in the conversations, you know, when you’re thinking about the next direction in your product, how are you going to make that decision? When you’re talking about decision making, you’re going to hear those types of things, right? If you hear like, oh, I’m just going to go with what I think is the right thing, you know, that could be a red flag. Maybe not, but it could be, right? So you really want to back founders who say, you know what, I’m a huge believer in data. Here’s how I get the information I need to make the decisions I need to make. And, you know, I think that just goes a long way. I think the other thing that I that I look for in a founder as I’m thinking about making investment is how good are they at sales? Most founders don’t come from a sales background. It’s very few and far between. And yet that’s going to be the most important thing that they do for their company early on. They’re almost always going to be the first people selling the product. How do they think about it? Can they wrap their head around it? Do they have curiosity around the process? What’s going to work? What’s not going to work? What do they do if they run into issues? And so as I have been in venture now for seven years, that’s one of the most important things I look for in a founder is how do they view the sales process and do I think they’re going to be able to close deals?
Brian Bell (00:18:26):
So you sat on lots of boards. What’s an experience, story, conversation that kind of changed your thinking about company building?
Karen Page (00:18:33):
So one example that I have is I was talking to a founder who was trying to get a really big deal closed. And in the conversation with her, she’s like, I just don’t know what to do. I’ve tried everything. They’re ignoring my emails. They said they were going to do this. They didn’t do it. I just don’t know. what my next step is. And I said, what do you have access? Do you know that the assistant’s email address? And she said, yeah, I think I do. I said, why don’t you just reach out to the assistant? And it was such a small thing and certainly not brilliant, not like one in a million, just kind of a basic sort of an approach that was outside of the typical process. And it It turned out to be what unlocked that deal. She wrote it to the assistant. The assistant gave her some time. She got time in front of the person she needed to get. We closed that deal. And it also was the foundation of building a platform with this customer for relationships across various areas. So sometimes it’s just a small little thing that, again, might be outside of the direct line of vision of the person who’s kind of working. You get lost in the big picture. And sometimes it’s just the simplest thing that can make a big difference. I’ve had some incredible board experiences where we’ve seen inflection points, whether it’s a potential sales process, whether it’s a CEO who might need to be transitioned out, whether it’s a CEO who wants to be transitioned out. And all of these things, I think I might be jumping around just a tiny bit, but... They all are predicated on trust. You know, nothing in any of these relationships will happen without a respected, trusted relationship between the board members and the team at the company, predominantly the CEO.
Brian Bell (00:20:25):
So you were at Box and it’s formative years and, you know, not that they’re not formative anymore, but definitely in the kind of that transition from, hey, Box is going to build its own cloud to, okay, maybe we should just kind of migrate to another cloud. That’s a big transition that we all went through, you know, 10 or 15 years ago. How does this AI transition kind of feel compared to that? You know, because you were very much in the operator seat back then and you’re in the kind of more advisor board member seat now, investor seat now. What are some commonalities in this kind of platform shift or how does it feel different, if at all?
Karen Page (00:20:57):
Yeah, I mean, the commonality is that it’s a fundamental platform shift. And people need to change the way that they view the world from a business perspective in order to stay with the wave. You always have early adopters, laggards, people you are just never going to adopt. And you have a myriad of perspectives whenever there’s a big shift. We are in a massive shift today. I think there are a ton of similarities, and I think that there are some big differences. I think the AI shift is magnificently larger than the cloud transition. And most companies have gone through their digital transformations and have figured out how to use AWS and all of these other platforms to run their businesses. But today, there’s an opportunity not just to is to shift where you store things and to shift how you hold your data. But now you have the ability to completely redefine processes and how people work. I think it sounds very easy when you say that, but when I think about like, you know, you go to a bank and you need to withdraw money and they say, well, you need to fill out this form. And you say, well, I don’t wanna fill out the form. You already have all my information. This is a waste of time. And they’re like, that’s the process. That’s what we have to do. And if you go talk to those people and say, what would work better? How could we change this? And who knows? They might come up with something that’s like, well, if we just have their ID, we know who they are, then we can do all of it without any paperwork because we have all this information. Well, that’s a redefined way of banking and it makes everybody’s job a lot easier. But I think that the work really is in how do we redefine this work, you know, and how do we use AI to do that? I think it’s going to be an incredible opportunity as we go through this transition process. I think it’ll take a little while. I think it’s going to be very interesting for companies that are kind of from the just pre-AI era or the non-AI native companies. But I think Fox has done a brilliant job. Several of the companies in my portfolio, I think, have done a brilliant job of integrating, of agentic tools of helping their clients use their data with AI in all different sorts of ways. So I think we’re going to be in a period of flux. I think we were in a flux for when we did the transition to the mobile era, when we transitioned to the cloud era, we see a couple of years of like, oh my gosh, what are we going to do? And that’s probably where we are with AI, but we’re going to move into this next era and it’s going to be transformational. I’m excited.
Brian Bell (00:23:26):
Yeah, and it’s happening faster than any previous platform shift. I think probably the closest would be going from paper and pen or pencil to like kind of PC. You know, doing stuff on computers or terminals. That was probably a pretty big transition back in the 70s and 80s. You know, and that took, you know, roughly 25 years to kind of play out. And I feel like AI is playing out in five or 10 years, most likely. So it’s going to be a much bigger platform shift, much faster, much more profound. And I’m seeing it as an early stage investor, you know, just with the tools and all the platforms our portfolio companies are building is just, wow, that’s incredible. I think, you know, shifting back to go to market, as you kind of advise companies around sales led motions or product led motions, or maybe even AI assisted models, how do you kind of think about building companies and advising them on what to do, especially as they hit a kind of A and they got a little product market fit and they’re looking to scale and how do you help them think through that?
Karen Page (00:24:22):
yeah complicated right now in some respects i think that you know a lot of the larger companies in our portfolio are still very much in the sales-led process and at the end of the day i think when you get to be a a company of size and substance that’s probably what you have to do i mean you can’t just go sell to google or nvidia or apple even without a process you can get started. I think we’re certainly seeing a resurgence of product-led growth, of people finding tools that solve their problems and they’re just adopting them. I also think that it’s a much more accepted practice today, even at larger companies, for teams to find and use the tools that solve the problems that they’re facing in getting their jobs done. I can’t help but think of a company like Lovable who is growing at an exponential speed because they’ve got this incredibly simple ZDU’s tool that is, you know, solving problems easily. But I think, you know, while product-led will get you into an organization, it’s not going to be something that helps you solve a, you know, company-wide type of a problem or a solution. So I think we’re going to see the evolution of that. The way that companies are selling right now certainly has changed. The way companies are marketing has certainly changed. That evolution is going to be really fun. And I do think that teams that are using like AI driven SDR tools are learning a lot from the experiences and they’re going to learn where and when we need to have a real person in the loop.
Brian Bell (00:25:53):
Yeah. I mean, I was talking to my wife about this because she has an AI startup and one of the things she’s struggling with is, okay, you know, we got some PLG kind of going and maybe we should shift and, you know, sell into enterprise. So she’s kind of wrestling with this and she knows GTM. She ran GTM at LinkedIn. How do you, yeah, how do you advise, you know, your startups to think about that? Like when is the time to shift into enterprise mode or maybe go find some more product market fit in the PLG motion or do everything all at once? Or how do you know, you know?
Karen Page (00:26:22):
Well, okay. If you’re growing through PLG, then you’re going to see the companies that are coming in the door and you’re going to know whether they need more. If somebody comes in and they’re like, yeah, we need a thousand seats. And by the way, seats are probably going to be something that, you know, we have to flip around and, you know, may go by the wayside as well. You know, you’re going to see who’s coming in your door. You’ll be able to make some good visions based on what you’re seeing. If you’re seeing a Google come in and wanting to buy, you know, a thousand seats, you’re going to need somebody who’s going to guide them through that. most likely even with the simplest of products so i think some of it will inform itself
Brian Bell (00:26:56):
yeah and i think you you touched on something that i want to tease out and pull the thread on which is kind of the thesis around gtm and pricing in an ai first world right because i i think i think the cloud was kind of our first kind of semblance of this where hey i could just pay for what i use as i use it right you know in ai there’s more outcome-based pricing right where it’s like hey i’m paying for the job to be done here and you’re deflecting you know this call you know in the call center and i know the cost of that five or 10 minute call and if you can deflect that for me i will pay you some percentage of that if you save me money and you do it as good of a job like how do you what’s your current thesis around this is ai is now you know eating labor right?
Karen Page (00:27:41):
Yeah. Yeah, I mean, we’re all on the go-to-market side eating some popcorn around this. The best companies, no matter the era, have a crisp, undeniable value proposition. Clarity is always going to win on this. The pricing approach, I think, will evolve. It’s most likely going to be not a per-seat basis. It’s going to be some sort of combination of usage. Some of it will depend on how much integration is actually needed. Larger corporations almost always will need some sort of an integration. I hope we don’t get to the point where we’re Salesforce all over again, where it’s a year process in order to get something launched. Hopefully we’ll be able to streamline those processes and pricing will match. We have to be able to be creative around that. I’m talking to a lot of my companies about how they’re thinking through it right now and lots of different models on the table. I think that we’ll see a little bit of experimentation and we’ll see where we land.
Brian Bell (00:28:31):
Yeah. Yeah. Yeah. It’s exciting time. Lots of, you know, it’s kind of like we shape our tools and our tools shape us and kind of the same thing goes in business, right? We shape this new tool and it’s shaping how we do business, right? How we price things, how we take things to work and how we build things. What are you seeing in your portfolio companies in terms of, you know, acceleration and capital efficiency and kind of this age of AI? Yeah. I could tell you in the early stages I’m seeing, particularly at the pre-seed, I see companies getting more traction before they raise and then they’re getting more traction per dollar spent. I’m wondering if you’re kind of seeing that too as you kind of go into the A and B and beyond.
Karen Page (00:29:05):
Yeah, I’m definitely seeing that as well. We’re also seeing a larger than previously seen number of companies being preempted, taking in more capital than we need, which is probably fueling some of the conversations around, you know, the bubble or no bubble. And, you know, That’s okay. Capital efficiency is trendy right now. We’re seeing capital efficiency be something that people use as a hallmark of their business and understanding, you know, the value per employee is a metric that’s becoming more and more important. I stand behind that. I think that’s a great metric to look at. And sometimes we get caught on the hamster wheel of ARR, CARR, you know, what is your monthly expectations? Did you actually hit it? Did you not hit it? As we change our pricing models, it’s going to be more like how much value can we create on the teams that we have? So I think that’s a really interesting trend as well.
Brian Bell (00:30:01):
Yeah, I wrote an article on this recently because, you know, AI is eating software and it’s eating labor and, you know, it’s doubling or tripling capital efficiency. And I don’t think people appreciate this, but, you know, AI and all the things that AI does, you know, all the cognitive tasks could be 10 to 30 or 50 X larger than SAS was, right? which is pretty breathtaking if you think about it. And all the repercussions for venture capital and the startup ecosystem, which means that we could end up in a situation where, you know, venture capital is like, what, $180 billion a year right now deployed? We could end up, you know, venture capital could end up being, you know, a trillion a year, right? Because it’s eating more and more of the economic pie and growing that pie, right? And generating more value, right? And growing GDP faster. Right.
Karen Page (00:30:49):
Right.
Brian Bell (00:30:50):
So very exciting time to be a VC or founder for that matter. I wish I was a founder. I’m just too deep in being a VC now.
Karen Page (00:30:57):
You can live vicariously through your wife.
Brian Bell (00:30:59):
Exactly. No, yeah, we have a founder in the family. Exactly. So I kind of get to talk to her about it every day. And what’s a theme that you’re a startup theme that you’re bullish on that most people are still overlooking?
Karen Page (00:31:09):
I really still like vertical software. I was just on a panel with the team at Workday a few weeks ago, and we were talking about, you know, some of their new products. They’re really intent on going smaller. I think it’s called Workday Go. They want to A lot of companies are like, we want to go to the enterprise and Workday right now is going, we want to go to SMB. And that’s great, but it doesn’t allow, even if a company like Workday focuses on an SMB, it doesn’t allow them to have the specialized solution set for verticalized companies. So I invested in a company named Goose. They are in the pet care industry, which is a massive space right now. You’ve got two dogs. I’ve got two dogs. You know, everybody loves their animals.
Brian Bell (00:31:53):
They’re not my dog. They’re not my wife’s dogs.
Karen Page (00:31:55):
Please. I can tell by a smile on your face. You love those dogs.
Brian Bell (00:31:58):
No, they’re not. I don’t. Don’t tell her that.
Karen Page (00:32:01):
I can see it in your eyes. She knows it, too.
Brian Bell (00:32:04):
So the deal was the deal was when we got the second dog, I agreed to get the first dog for the kids. This is five years ago. And, you know, a year or two later, let’s get another dog. I’m like, OK, here’s the deal. Dogs are a lot of work. I don’t want it. Like if we get a second dog, I don’t want anything to do with that dog. Like the kids, you guys got to take care of it. Right. So that was like that was the deal. And of course, like my wife basically takes care about the dogs. Right.
Karen Page (00:32:27):
Oh, that’s pretty good. I bet both dogs, you know, the kind of dogs, they smell in you that you have a little bit of resistance. So they jump on your lap. They snuggle up. Yeah.
Brian Bell (00:32:36):
Well, we just had to replace the couch, right? You know, we have this five-year-old couch, four-year-old couch. And they just, you know, they’re like not very house trainable. And unless you keep an eye on them 24-7, they’ll just pee wherever. And so eventually we’re just like, we didn’t have waterproof covers on the couch. And so eventually we’re like, This couch stinks. I think people come over and they just smell dog, right? Dog pee. And so we had to just replace our whole like a four-year-old couch. Anyway, let’s talk about boardrooms and government.
Karen Page (00:33:01):
Do you want me to circle back to, we were talking about vertical software.
Brian Bell (00:33:06):
Oh, yeah. I love vertical. Yeah. I’m also very bullish on vertical. But yeah, finish your thought there.
Karen Page (00:33:10):
All right. I’ll go back to that. Workday Go is trying to go into the SMB, but they can’t have the type of solutions that cover the breadth of the services. So I invested in this company called Goose, which is in the pet care space. They work, they provide verticalized software to solve all the problems for groomers and boarding companies, which is fantastic because previously you had to have somebody at the desk who was answering the phone. Today we can take care of all of that. You can make money 24 seven. And it’s just a game changer. They’re using AI to do very simple things like sending a note to the owner saying like Mocha was a good girl today. And, you know, it’s really transformative. So even solutions that are aimed at solving the companies that most businesses face aren’t going to solve the problems that vertical solutions can really dig into. So I’m very bullish on that space. And there’s a massive number of companies that would benefit.
Brian Bell (00:34:03):
Yeah, and I think the thing to build on what you’re saying, and I agree, is that people don’t realize is that there’s lots of verticals where previously the market was not big enough to really create a billion dollar company in SaaS. But again, back to my previous comment, SaaS was, you know, one, two, maybe 3% of your total revenue typically is what you would spend on your software. depending on the software stack or whatever, now that you can layer AI into all these cognitive abilities, all these cognitive tasks in the vertical stack of all, like in pet care, right? And I’m in some vet platforms as well. You can eat a bigger share of the total revenue, right? You can eat up more labor on the operating budget.
Karen Page (00:34:43):
Yes.
Brian Bell (00:34:44):
And so now you can create more revenue in that vertical or eat up more revenue or generate more value and capture more value and create a bigger company. So I’m very, I’m very bullish on like vertical AI, like AI applications, agentic workflow, stuff like that for the for the same reason.
Karen Page (00:34:59):
Right, right. And then the cool thing is, is that I think what we’ll see is that the value add there is in shifting from the generic type of a solution that you might get from, you know, a larger company into really helping very specifically tweak things to improve the quality of business.
Brian Bell (00:35:18):
Yeah, OpenAI is not going to create a verticalized pet platform, right? They’re just not going to go after that space, right? But you can leverage their APIs and their tools and their agent web or whatever it’s called.
Karen Page (00:35:29):
Yeah, agent force, yeah, sales force.
Brian Bell (00:35:31):
So you’re known for helping founders scale themselves. What does that look like in practice?
Karen Page (00:35:35):
Gosh, let’s see. I really, I really hope that I offer, you know, high quality advice and overall help to, to the founders. I really hope that I’ve helped build companies that will last, not just because of the products, but because of the leaders who built them. And, you know, I really hope that I’ve contributed over time to the types of cultures that, that build high quality, not only governance from a governance always sounds like such a, you know, kind of a, lawyer or accountant type of a word,
Brian Bell (00:36:06):
but I really think that- Bureaucracy is what it sounds like to me.
Karen Page (00:36:08):
Yeah, it sounds like bureaucracy. So I don’t want it to sound that way, but I mean sort of like the rules that we run the businesses by. What do we stand for? And I hope in the companies that I work with that we have a strong desire and ability to build culture and that we are focused on elevating our leaders and providing them with access to the tools that they need to grow and to be super successful. I hope the founders know that we are right by their side willing to go through this and to help them in any way that they need. I also really hope that for my founders, that they find in themselves the ability to scale themselves as much as their companies, that over time, through their curiosity and through their learned experiences, that they’re really creating for themselves this vast library of experiences and and also their broader network who is there to support them as they continue to grow.
Brian Bell (00:37:06):
So there’s founders out there that don’t have a board, right? They’re pre-seed, they’re seed, and they don’t even have a board yet. When should they think about constructing a board? How should they construct it? And what are some kind of gotchas and things to watch out for?
Karen Page (00:37:19):
Yeah, you know, the pendulum swing is, you know, it goes from people who want to have a board as soon as they raise any money all the way to I’m going to wait until I raise the Series A and see how it goes there. There are certain investors like Shruti at Array who wants it. She wants a board the moment that she funds a company and she’s generally first money in. So there’s some variations on thoughts around this. I like to see a board at Seed. but not all of the founders do. If that’s what the founder wants, then we’ll do it. If they want to wait till A, we’ll go that route as well. What I do with founders before there is an official board is we have mock boards. We get together with founders, we talk about the business. I still firmly believe that while it’s very important for me to have weekly, monthly, whatever the cadence is, calls with the founder to see what’s going on in the business, see what they need, see if there’s anything I can be doing to be helpful. I’m I also really believe that it’s helpful to have the other investors around the table as well, because I might say, hey, I think this is what would be a good outcome here. I think this is what we ought to do. The other investor might say, you know what, I’ve got another company in the space right now. They just found that that wasn’t a great way to approach it. Let’s talk about two other things we could do instead. So I like the idea of having kind of a room full of trusted advisors that the CEO can take what they believe they need from.
Brian Bell (00:38:40):
What do you wish more founders asked of their investors and board members?
Karen Page (00:38:43):
I’ve seen founders who neglect to pull their boards in early enough in certain scenarios. And the scenarios can vary greatly. One could be, you know, we hired this guy six months ago. I’m not sure they’re really being, they’re not as effective as I think they ought to be. What do you think I ought to do? I mean, that’s a very simple one. Sometimes the CEOs don’t do that. That’s an easy way to get your board around the table or one board member around the table others are indications that you know things are either inflecting up or maybe not maybe down let’s get a conversation going don’t wait you know don’t wait to call me i don’t want to hear just the fluff and the beautiful things although i do really like that part i want to be brought in when i when i can hopefully hopefully drive something down a different path and make it make a better outcome
Brian Bell (00:39:33):
yeah ask for help earlier how do you look let’s talk about kind of uh looking forward how do you see venture evolving in the next you know five years or so you
Karen Page (00:39:42):
know venture has it’s so funny how many people are speaking out on their point of view on venture what’s working what’s not working is it too big is it not big enough is you know going only towards emerging founder or emerging funds um you know, et cetera, et cetera. I think venture is going to adapt. I think we have over the past several decades and will continue to adapt. I think probably the most notable thing I would say is that, you know, we have some very, very large prominent venture funds out there and we’re seeing some people break away and take off and start their own funds. They are generally speaking, not having difficulty raising money from LPs because of their association affiliation with some of the big names. And I think those funds are going to be funds to watch. I I think we’re going to see different ideas, different approaches, and different ways to collaborate emerge from that. I really love funds who get very deep into the relationships with the founder, the founder networks, and build their investment thesis around their communities. I love when a GP can say, I sourced this founder from my community. I’ve known him for five years. I’ve known her for five years. My network knows this person. And there’s going to be a tight relationship built that’s going to guide the company. I love seeing that. I think there’s a lot of impact there.
Brian Bell (00:41:13):
Yeah. Yeah, the way we do that at Team Ignite is we, yeah, basically leverage our community and network. It’s not me, the GP, helping anyone or sitting on any boards. It’s like me being the conduit of like, hey, you should talk to this person to help with that. Because I’ve realized I’m not really good at anything. That’s kind of what differentiates me.
Karen Page (00:41:32):
I don’t buy that. But think about it. Like mostly, for the years that I’ve been at Venture, you know, deals come much from a network of their venture partners. venture capitalists as it has from a community that I’ve built. And I think seeing that spin around just a little bit is is a very interesting take.
Brian Bell (00:41:52):
Now, let’s take the other side of the coin. You know, how do you see startups evolving over the next five years?
Karen Page (00:41:57):
Sort of to what we had said earlier, we need founders who understand the dynamics of the business, not only how are they going to get their product in market, how do they understand and assess the early signs of growth in either direction? How do they hire the best teams? I think talent is an impossible situation today. I know a young woman who is a an engineer recruiter at a very large public firm. And she was saying like, we’re offering million dollar sign-on bonuses and we can’t get them to sign on. So the talent wars on the engineering slash AI side are gonna continue to get tough. So we have to nurture an environment of engineers and people, which I think the universities do, of really wanting the experience of being on a small team and building something. because it’s so easy to go to a large corporate and make a ton of money and maybe have fascinating experiences. But I think we still have to come back to, we need to nurture builders and make it viable for founders to be able to bring good talent on.
Brian Bell (00:43:03):
Yeah, I think there’s probably an opportunity there. If you’re willing to pay, throw millions of dollars at people to get talent, there’s probably an opportunity to go upstream and develop talent, right?
Karen Page (00:43:13):
I agree.
Brian Bell (00:43:13):
Just train people. Find a smart person that’s doing something ancillary or kind of related to what you need. And then AI moves so quickly that you can just train them in a few months, if they’re really smart, to start doing the thing. This is kind of what happened, you know, 10 years ago with like all the coding boot camps and go, you know, be a developer in 90 days. It’s like, it doesn’t make sense to go get a four or five year CS degree to go be, you know, to go build like full stack stuff. You could just like learn it in 90 days and get on the job training, you know?
Karen Page (00:43:44):
Right. Yeah. Yeah. I mean, you and I both said we got the startup, you know, years and years ago. That’s what we need to facilitate is how do we get people really excited to be, you know, to be on the inner workings of something that’s going to be massive. Yeah.
Brian Bell (00:43:58):
Well, let’s wrap up with some quick questions. What’s a GTM principle you think will never change?
Karen Page (00:44:03):
I think it’s going to be around clarity. What are you selling? Who are you selling it to? Why is it going to change the way that their business succeeds and change the way that their teams embrace their roles? So I think the best companies, no matter what era we’re in, are going to have a crisp, undeniable value proposition and clarity always wins. You can change channels, you can change tactics and tooling, but if you can’t articulate your value in a way that the customer immediately understands, I think nothing else matters. So I think that’ll stay the same as we move forward.
Brian Bell (00:44:34):
Which founder or company surprised you in a good way and why?
Karen Page (00:44:37):
You know, I’m consistently impressed when a founder can demonstrate real self-awareness at a critical moment. One recent example for me was a CEO who recognized early that their company needed a different type of go-to-market leader for the next stage of scale. And this is a company that’s already, you know, doing hundreds of millions in revenue. So it was a big revelation and a very difficult decision because of the impact that it would have on the broader organization. But making that call early, while it’s uncommon, to me also signaled maturity and long-term thinking.
Brian Bell (00:45:12):
What’s a boardroom lesson you wish you had learned earlier in your career?
Karen Page (00:45:16):
I don’t think I was ever at a point in time where I didn’t realize this. So it wasn’t like I had to learn it per se, but I think the importance of it has continued to elevate. And that is that, you know, trust is built from the very first meeting, the very first time you, you meet a founder or a team. I wish I had understood sooner how much the tone and the cadence and the expectations set in those early conversations really shape throughout the growth of the company and every hard discussion that comes and they all come that You always have a hard conversation. The underlying foundation of trust that is built early really carries those conversations forward. Really, the impact on the team, on the founder, on the board, when there is trust and understanding that everybody’s working to the same goal is irreplaceable. So I think that’s really important.
Brian Bell (00:46:06):
Which of your portfolio companies best represents where enterprise software is headed?
Karen Page (00:46:10):
I think I have a variety of companies that probably preclude one answer to that question. One company that I am particularly thrilled with right now is a company called Overstory. It’s in the vegetation management space. They work with utility companies to protect against forest fires. So not only do I think that’s a wildly important cause to address, it’s also wildly complicated to enact. So they are taking many complicated systems to put together to solve this problem for utility companies. And not only that, they’ve got a much broader intention, much broader mandate to achieve. So I think it brings to mind for me the idea of building the plane while you’re sailing off a cliff and all of those other ideas. So how can you continue to sell, continue to make sure the company is well-funded and well-run, has the right people in place while also creating an expansive platform platform that’s going to solve some of the most critical problems we’re facing as an ecosystem.
Brian Bell (00:47:13):
What’s the hardest board decision you’ve ever had to make?
Karen Page (00:47:16):
Those decisions are always around teams. You know, is the CEO doing what they need to be doing? If they’re not, what are we going to do about it? Do they need coaching? Do they need training? Or is it time to consider a new leader? Again, that’s where the hard conversations have to happen. And if you don’t have good relationships with the other folks on the board, it makes it very, very difficult to create consensus. and a plan that’s gonna work moving forward. So I think people conversations and people decisions are typically the hardest on a board.
Brian Bell (00:47:47):
How do you think investors should redefine value add in the era of AI powered founders? And what I mean by that is we have this 150 IQ, you know, chat GPT pro we can ask any question to, like, how should investors kind of think about adding value now that you, you know, and the AI is only gonna get an order of magnitude better every year or two. So where do we go from here as investors?
Karen Page (00:48:07):
You know, I don’t think much will change on that part. What do we provide? Hopefully we’re providing strategic insights. That’s not going to be replaced by AI. It’s going to maybe change the conversation. But the ultimate decisions are still going to be forced by strong judgment. And that’s not going to be something that we see AI doing. take on anytime soon. The other thing are the connections that we have. As people, it’s about, you know, I know the head of product at Microsoft, or I’m really good friends with this leader at this other venture fund who you should meet to see if they’d like to invest as well. So I think a lot of it is just around the judgment calls, the strategic inputs, and the resources that we provide as investors.
Brian Bell (00:48:47):
Yeah, I’ve been thinking about this a lot. That’s why it’s in there. Last question. So when you zoom out decades from now, what impact and legacy do you hope you had in your career and life?
Karen Page (00:48:56):
Well, the one thing I want to say is, you know, ultimately, it’s I hope I’ve created businesses that last. But, you know, at Box, we rang the bell at the NYSE on stage. And I can’t help but say I’d love to have that experience again.
Brian Bell (00:49:11):
You were on the stage when it happened?
Karen Page (00:49:12):
Oh, yeah.
Brian Bell (00:49:13):
Oh, that’s amazing.
Karen Page (00:49:14):
That was one of the most incredible experiences of my life. And I tell my founders that we should do that again because it’s pretty fun. I hope I have, you know, helped create companies that last because they built great products and because of the leadership that built the products, you know, the teams that have stood behind them. And, you know, I hope I’ve helped to create cultures that are built on clarity and trust and, you know, help founders scale themselves as much as their companies.
Brian Bell (00:49:38):
Well, this has been an amazing conversation, Karen. I learned so much. Thanks so much for coming on.
Karen Page (00:49:42):
It was great to be here, Brian. Thank you so much.
Brian Bell (00:49:44):
Thank you.
